Angewandte Chemie International Edition

Cover image for Angewandte Chemie International Edition

September 27, 2013

Volume 52, Issue 40

Pages 10391–10660

  1. Cover Pictures

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. You have free access to this content
      Cover Picture: Biosynthesis of the Antimetabolite 6-Thioguanine in Erwinia amylovora Plays a Key Role in Fire Blight Pathogenesis (Angew. Chem. Int. Ed. 40/2013) (page 10391)

      Dr. Sébastien Coyne, Dr. Cornelia Chizzali, Mohammed N. A. Khalil, Agnieszka Litomska, Dr. Klaus Richter, Prof. Dr. Ludger Beerhues and Prof. Dr. Christian Hertweck

      Article first published online: 4 SEP 2013 | DOI: 10.1002/anie.201307309

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      Fire blight, a devastating plant disease that mainly affects apple and pear trees, is caused by the bacterium Erwinia amylovora. In their Communication on page 10564 ff. C. Hertweck et al. unveil a key role of the antimetabolite 6-thioguanine in fire blight of apple plants. Biosynthetic studies indicate that the protein YcfA mediates guanine thionation in analogy to 2-thiouridylase. (The authors thank Nico Ueberschaar for his contribution to the cover picture.)

    2. You have free access to this content
      Inside Cover: Positron Emission Tomography Imaging of Drug-Induced Tumor Apoptosis with a Caspase-Triggered Nanoaggregation Probe (Angew. Chem. Int. Ed. 40/2013) (page 10392)

      Dr. Bin Shen, Dr. Jongho Jeon, Dr. Mikael Palner, Dr. Deju Ye, Dr. Adam Shuhendler, Prof. Frederick T. Chin and Prof. Jianghong Rao

      Article first published online: 20 AUG 2013 | DOI: 10.1002/anie.201306442

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      The caspase-3 activity in doxorubicin-treated tumor xenografts is studied by positron emission tomography (PET) using a novel 18F-labeled caspase-3-sensitive nanoaggregation tracer. In their Communication on page 10511 ff., J. Rao, F. T. Chin, et al. show that the enzyme-activatable tracer improves the PET imaging of apoptotic tumors by intramolecular macrocyclization and in situ aggregation of the cyclized tracer upon caspase-3 activation. (Picture: Jim Strommer and Lydia-Marie Joubert.)

    3. You have free access to this content
      Inside Back Cover: (Angew. Chem. Int. Ed. 40/2013) (page 10659)

      Dr. Yulia V. Gerasimova and Dr. Dmitry M. Kolpashchikov

      Article first published online: 4 SEP 2013 | DOI: 10.1002/anie.201307181

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      PCR-free RNA detection from whole cells can be achieved using a multitude of short functional DNA staple strands that form an associate with target RNA that produces a fluorescent signal. In their Communication on page 10586 ff., Y. V. Gerasimova and D. M. Kolpashchikov explain how this method can be used as a simple and rapid assay for the detection of bacteria in clinical, food, or environmental specimens.

    4. You have free access to this content
      Back Cover: Rapid, Isothermal DNA Self-Replication Induced by a Destabilizing Lesion (Angew. Chem. Int. Ed. 40/2013) (page 10660)

      Abu Kausar, Catherine J. Mitran, Yimeng Li and Prof. Julianne M. Gibbs-Davis

      Article first published online: 20 AUG 2013 | DOI: 10.1002/anie.201306894

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      Like clockwork, rapid isothermal self-replication of oligonucleotides can be achieved using a cross-catalytic strategy as reported by J. M. Gibbs-Davis et al. in their Communication on page 10577 ff. The presence of both a destabilizing lesion in one of the replicating fragments and concentrated DNA polymerase results in high reaction rates and are key to multiple replication cycles (Photo by Dean Albrecht).

  2. Graphical Abstract

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Graphical Abstract: Angew. Chem. Int. Ed. 40/2013 (pages 10395–10409)

      Article first published online: 23 SEP 2013 | DOI: 10.1002/anie.201390041

  3. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
  4. Author Profile

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Stephan A. Sieber (page 10416)

      Article first published online: 6 MAY 2013 | DOI: 10.1002/anie.201303078

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      “I lose track of time when I climb a mountain. My biggest motivation is to reach the summit. …” This and more about Stephan A. Sieber can be found on page 10416.

  5. News

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
  6. Obituary

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Haldor Topsøe (1913–2013) (page 10418)

      Jens K. Nørskov and Bjerne S. Clausen

      Article first published online: 13 SEP 2013 | DOI: 10.1002/anie.201306691

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  7. Book Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Spin-Crossover Materials. Properties and Applications. Edited by Malcolm A. Halcrow. (page 10419)

      Andreas Hauser

      Article first published online: 13 AUG 2013 | DOI: 10.1002/anie.201306160

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      John Wiley & Sons, Hoboken, 2013. 564 pp., hardcover, € 149.00.—ISBN 978-1119998679

  8. Highlight

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Membrane Transport

      The Tricky Task of Nitrate/Nitrite Antiport (pages 10422–10424)

      Prof. Susana L. A. Andrade and Prof. Oliver Einsle

      Article first published online: 9 AUG 2013 | DOI: 10.1002/anie.201305421

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      Subtle differences: Two recent crystal structures have provided the first insight into nitrate/nitrite exchangers (example shown with bound nitrite), which are crucial to bacterial metabolism. A direct comparison of the structures reveals how the proteins can distinguish between their highly similar substrates and translate this into a conformational change to translocate ions across the membrane.

  9. Minireview

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Artificial Photosynthesis

      Water-Splitting Catalysis and Solar Fuel Devices: Artificial Leaves on the Move (pages 10426–10437)

      Dr. Khurram Saleem Joya, Dr. Yasir F. Joya, Prof. Kasim Ocakoglu and Prof. Roel van de Krol

      Article first published online: 19 AUG 2013 | DOI: 10.1002/anie.201300136

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      Turning a new leaf: Electrochemical and light-driven electrocatalytic water oxidation assemblies have been targeted to develop artificial photosynthetic system. Such “Artificial Leaves” are used to make H2 and O2 using water as a raw material. The design and performance of the water oxidation systems and standalone solar-to-fuel conversion devices are presented. Progress in the field and future perspectives of water splitting are also discussed.

  10. Review

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. Electrochemistry

      Bipolar Electrochemistry (pages 10438–10456)

      Stephen E. Fosdick, Kyle N. Knust, Karen Scida and Prof. Richard M. Crooks

      Article first published online: 10 JUL 2013 | DOI: 10.1002/anie.201300947

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      A bipolar electrode is a single conductive object that drives both electrochemical oxidations and reductions simultaneously. They have been used for many important applications and advances, for example, in sensors or as mobile electrodes that are able to move freely in solution.

  11. Communications

    1. Top of page
    2. Cover Pictures
    3. Graphical Abstract
    4. News
    5. Author Profile
    6. News
    7. Obituary
    8. Book Review
    9. Highlight
    10. Minireview
    11. Review
    12. Communications
    1. High-Pressure Zeolites

      Synthesis of a Novel Zeolite through a Pressure-Induced Reconstructive Phase Transition Process (pages 10458–10462)

      Dr. Jose L. Jordá, Prof. Fernando Rey, Dr. German Sastre, Dr. Susana Valencia, Miguel Palomino, Prof. Avelino Corma, Prof. Alfredo Segura, Prof. Daniel Errandonea, Dr. Raúl Lacomba, Prof. Francisco J. Manjón, Dr. Óscar Gomis, Dr. Annette K. Kleppe, Prof. Andrew P. Jephcoat, Dr. Mónica Amboage and Dr. J. Alberto Rodríguez-Velamazán

      Article first published online: 1 AUG 2013 | DOI: 10.1002/anie.201305230

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      The first pressure-induced solid-phase synthesis of a zeolite has been found through compression of a common zeolite, ITQ-29 (see scheme, Si yellow, O red). The new microporous structure, ITQ-50, has a unique structure and improved performance for propene/propane separation with respect the parent material ITQ-29.

    2. Supramolecular Chemistry

      Backbone-Directed Perylene Dye Self-Assembly into Oligomer Stacks (pages 10463–10467)

      Dr. Changzhun Shao, Dr. Matthias Stolte and Prof. Dr. Frank Würthner

      Article first published online: 13 AUG 2013 | DOI: 10.1002/anie.201305894

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      Arm wrestling: Backbone-directed “arm-to-arm” aggregation of a newly designed perylene bisimide (PBI) dyad with a defined intramolecular space leads to the growth of kinetically stable extended PBI π-stacks. This PBI dyad was shown to assemble into oligomers up to 21 units in length.

    3. Functional Particles

      Microscale Polymer Bottles Corked with a Phase-Change Material for Temperature-Controlled Release (pages 10468–10471)

      Dr. Dong Choon Hyun, Dr. Ping Lu, Dr. Sang-Il Choi, Prof. Unyong Jeong and Prof. Younan Xia

      Article first published online: 20 AUG 2013 | DOI: 10.1002/anie.201305006

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      Keep your wine chilled! Microscale polystyrene (PS) bottles are loaded with dye molecules and then corked with a phase-change material (PCM). When the temperature is raised beyond its melting point, the PCM quickly melts and triggers an instant release of the encapsulated dye. The release profiles can be manipulated by using a binary mixture of PCMs with different melting points.

    4. Total Synthesis

      Synthesis and Determination of the Absolute Configuration of Cavicularin by a Symmetrization/Asymmetrization Approach (pages 10472–10476)

      Dr. Hiromu Takiguchi, Prof. Dr. Ken Ohmori and Prof. Dr. Keisuke Suzuki

      Article first published online: 16 AUG 2013 | DOI: 10.1002/anie.201304929

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      Taking the strain: The asymmetric total synthesis and stereochemical assignment of (−)-cavicularin, which features a highly strained polycyclophane ring system, has been achieved. The key features of this synthesis are 1) macrocyclization by an SNAr reaction, 2) group-selective reaction to induce planar chirality in a highly stereoselective manner, and 3) radical transannulation to construct the highly strained ring system.

    5. Inorganic Graphene Analogues

      Ultrathin Nanosheets of Vanadium Diselenide: A Metallic Two-Dimensional Material with Ferromagnetic Charge-Density-Wave Behavior (pages 10477–10481)

      Kun Xu, Pengzuo Chen, Xiuling Li, Prof. Changzheng Wu, Dr. Yuqiao Guo, Dr. Jiyin Zhao, Prof. Xiaojun Wu and Prof. Yi Xie

      Article first published online: 16 AUG 2013 | DOI: 10.1002/anie.201304337

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      A new metallic 2D material with high electrical conductivity (1×103 S m−1) consists of VSe2 ultrathin nanosheets with 4–8 Se-V-Se atomic layers. This is the first 2D transition-metal dichalcogenide with intrinsic room-temperature ferromagnetism. The nanosheets increase the charge-density-wave transition temperature to 135 K by dimensional reduction.

    6. Graphene Actuators

      Graphene Fibers with Predetermined Deformation as Moisture-Triggered Actuators and Robots (pages 10482–10486)

      Huhu Cheng, Jia Liu, Yang Zhao, Chuangang Hu, Dr. Zhipan Zhang, Dr. Nan Chen, Prof. Lan Jiang and Prof. Liangti Qu

      Article first published online: 14 AUG 2013 | DOI: 10.1002/anie.201304358

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      Enough to make your hair curl! Moisture-responsive graphene (G) fibers can be prepared by the positioned laser reduction of graphene oxide (GO) counterparts. When exposed to moisture, the asymmetric G/GO fibers display complex, well-controlled motion/deformation in a predetermined manner. These fibers can function not only as a single-fiber walking robot under humidity alternation but also as a new platform for woven devices and smart textiles.

    7. RNA Dynamics

      Efficient Detection of Hydrogen Bonds in Dynamic Regions of RNA by Sensitivity-Optimized NMR Pulse Sequences (pages 10487–10490)

      Dr. Andre Dallmann, Dr. Bernd Simon, Dr. Malgorzata M. Duszczyk, Hamed Kooshapur, Prof. Dr. Arthur Pardi, Dr. Wolfgang Bermel and Prof. Dr. Michael Sattler

      Article first published online: 14 AUG 2013 | DOI: 10.1002/anie.201304391

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      Improved Sensitivity: Efficient NMR experiments are presented for determining the secondary structure in large and dynamic RNAs using J-couplings across hydrogen bonds (see picture). The experiments provide up to eight-fold improved sensitivity and thus enable detection of base pairs in dynamic regions even in large RNAs.

    8. Organic Optoelectronics

      Dynamically Adaptive Characteristics of Resonance Variation for Selectively Enhancing Electrical Performance of Organic Semiconductors (pages 10491–10495)

      Ye Tao, Jianjian Xiao, Dr. Chao Zheng, Zhen Zhang, Mingkuan Yan, Dr. Runfeng Chen, Dr. Xinhui Zhou, Huanhuan Li, Dr. Zhongfu An, Zhixiang Wang, Dr. Hui Xu and Prof. Wei Huang

      Article first published online: 14 AUG 2013 | DOI: 10.1002/anie.201304540

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      Increased resonance: The selective tuning of the optoelectronic properties of organic semiconductors is possible by enantiotropic resonance variation. Using resonance forms of N+[DOUBLE BOND]P[BOND]O in a series of arylamine-phosphine oxide hybrids afforded low-voltage-driven phosphorescent OLEDs with outstanding performances.

    9. Synthetic Methods

      Versatile Synthesis of Benzothiophenes and Benzoselenophenes by Rapid Assembly of Arylzinc Reagents, Alkynes, and Elemental Chalcogens (pages 10496–10499)

      Bin Wu and Prof. Naohiko Yoshikai

      Article first published online: 19 AUG 2013 | DOI: 10.1002/anie.201304546

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      Rapidly aSSembled: The combination of cobalt-catalyzed migratory arylzincation and copper-mediated/catalyzed chalcogenative cyclization allows the construction of benzothiophenes and benzoselenophenes from arylzinc reagents, alkynes, and elemental chalcogens. Benzothiophenes and benzoselenophenes diversely functionalized at the benzene ring moiety can be prepared, which are not readily accessible by conventional methods.

    10. Supramolecular Chemistry

      {Mo24Fe12} Macrocycles: Anion Templation with Large Polyoxometalate Guests (pages 10500–10504)

      Dr. Xikui Fang, Laura Hansen, Fadi Haso, Dr. Panchao Yin, Dr. Abhishek Pandey, Prof. Dr. Larry Engelhardt, Dr. Igor Slowing, Dr. Tao Li, Prof. Dr. Tianbo Liu, Prof. Dr. Marshall Luban and Prof. Dr. David C. Johnston

      Article first published online: 13 AUG 2013 | DOI: 10.1002/anie.201304887

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      POM and circumstance: Nanometer-sized polyoxometalates (POMs) bring a new direction to anion-templated supramolecular chemistry. The Keggin (left) and Dawson-type (right) polyoxoanions direct the assembly of giant metallomacrocycles through an array of weak hydrogen-bonding interactions. The concerted action of multiple hydrogen bonds keeps the templating guests embedded within the hosts, even in the solution state.

    11. Mesoporous Materials

      A Resol-Assisted Co-Assembly Approach to Crystalline Mesoporous Niobia Spheres for Electrochemical Biosensing (pages 10505–10510)

      Wei Luo, Yuhui Li, Dr. Junping Dong, Jing Wei, Prof. Dr. Jiaqiang Xu, Prof. Dr. Yonghui Deng and Prof. Dr. Dongyuan Zhao

      Article first published online: 13 AUG 2013 | DOI: 10.1002/anie.201303353

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      Templated pores: A resol-assisted solvent-evaporation-induced self-assembly (RA-EISA) gives unique ordered mesoporous niobia spheres by using the amphiphilic diblock copolymer PEO-b-PS as a template. The mesoporous Nb2O5 spheres have ordered hexagonal structures, large pore size and high surface area, and a nanocrystalline framework (see picture). They show excellent electrochemical sensing of hydrogen peroxide.

    12. Radiopharmacology

      Positron Emission Tomography Imaging of Drug-Induced Tumor Apoptosis with a Caspase-Triggered Nanoaggregation Probe (pages 10511–10514)

      Dr. Bin Shen, Dr. Jongho Jeon, Dr. Mikael Palner, Dr. Deju Ye, Dr. Adam Shuhendler, Prof. Frederick T. Chin and Prof. Jianghong Rao

      Article first published online: 23 JUL 2013 | DOI: 10.1002/anie.201303422

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      Drug Design: An 18F-labeled caspase-3-sensitive nanoaggregation positron emission tomography tracer was prepared and evaluated for imaging the caspase-3 activity in doxorubicin-treated tumor xenografts. Enhanced retention of the 18F activity in apoptotic tumors is achieved through intramolecular macrocyclization and in situ aggregation upon caspase-3 activation (see picture).

    13. DNA–Protein cross-linking

      Vinylsulfonamide and Acrylamide Modification of DNA for Cross-linking with Proteins (pages 10515–10518)

      Jitka Dadová, Petr Orság, Dr. Radek Pohl, Dr. Marie Brázdová, Prof. Dr. Miroslav Fojta and Prof. Dr. Michal Hocek

      Article first published online: 12 AUG 2013 | DOI: 10.1002/anie.201303577

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      Bioorthogonal covalent cross-linking of DNA-binding proteins (p53) to DNA was achieved through novel DNA probes bearing a reactive vinylsulfonamide (VS) group. The VS-modified dCTP served as building block for polymerase synthesis of modified DNA, which was readily conjugated with cysteine-containing peptides and proteins by Michael addition.

    14. Alkyne Cyclization

      Photochemical Double 5-exo Cyclization of Alkenyl-Substituted Dithienylacetylenes: Efficient Synthesis of Diarylated Dithienofulvalenes (pages 10519–10523)

      Dr. Aiko Fukazawa, Takashi Karasawa, Dr. Hongyu Zhang, Kazumitsu Minemura, Dr. Cristopher Camacho, Dr. Jian Wang, Prof. Dr. Stephan Irle and Prof. Dr. Shigehiro Yamaguchi

      Article first published online: 13 AUG 2013 | DOI: 10.1002/anie.201303738

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      Smooth and selective: Upon photoirradiation, bis(3-alkenyl-2-thienyl)acetylenes smoothly and selectively undergo double 5-exo-dig cyclization to produce a series of thiophene-fused pentafulvalenes with various aryl substituents. In this fused π-conjugated skeleton, the fused thiophene rings and the aryl substituents significantly modulate the electronic structure of the pentafulvalene skeleton.

    15. Hydrogen Bonding

      Intramolecular OH⋅⋅⋅FC Hydrogen Bonding in Fluorinated Carbohydrates: CHF is a Better Hydrogen Bond Acceptor than CF2 (pages 10524–10528)

      Dr. Guy T. Giuffredi, Prof. Véronique Gouverneur and Dr. Bruno Bernet

      Article first published online: 19 AUG 2013 | DOI: 10.1002/anie.201303766

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      An intramolecular bifurcated H-bond from the axial HO-2 group to the axial F-4 atom and to the O5 atom of α-D-hexopyranosides in apolar solvents is evidenced in 1H NMR spectra. The H-accepting properties of the F atom are modulated by the orientation of the O-substituent at the C3 atom and by an additional F atom at the C4 atom (see picture).

    16. Nitrogenase

      You have full text access to this OnlineOpen article
      The Sixteenth Iron in the Nitrogenase MoFe Protein (pages 10529–10532)

      Dr. Limei Zhang, Dr. Jens T. Kaiser, Dr. Gabriele Meloni, Dr. Kun-Yun Yang, Dr. Thomas Spatzal, Dr. Susana L. A. Andrade, Dr. Oliver Einsle, Dr. James B. Howard and Dr. Douglas C. Rees

      Article first published online: 21 AUG 2013 | DOI: 10.1002/anie.201303877

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      Another iron in the fire: X-ray anomalous diffraction studies on the nitrogenase MoFe protein show the presence of a mononuclear iron site, designated as Fe16, which was previously identified as either Ca2+ or Mg2+. The position of the absorption edge indicates that this site is in the oxidation state +2. The high sequence conservation of the residues coordinated to Fe16 emphasizes the potential importance of the site in nitrogenase.

    17. Strong Coupling

      Thermodynamics of Molecules Strongly Coupled to the Vacuum Field (pages 10533–10536)

      Dr. Antoine Canaguier-Durand, Dr. Eloïse Devaux, Dr. Jino George, Prof. Yantao Pang, Dr. James A. Hutchison, Dr. Tal Schwartz, Dr. Cyriaque Genet, Nadine Wilhelms, Prof. Jean-Marie Lehn and Prof. Thomas W. Ebbesen

      Article first published online: 14 AUG 2013 | DOI: 10.1002/anie.201301861

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      The thermodynamics of strong coupling between molecules and the vacuum field is analyzed and the Gibbs free energy, the enthalpy, and entropy of the coupling process are determined for the first time. The thermodynamic parameters are a function of the Rabi splitting and the microscopic solvation. The results provide a new framework for understanding light-molecule strong coupling.

    18. Peptide Nanotubes

      Insights into the Molecular Architecture of a Peptide Nanotube Using FTIR and Solid-State NMR Spectroscopic Measurements on an Aligned Sample (pages 10537–10540)

      Prof. David A. Middleton, Dr. Jillian Madine, Dr. Valeria Castelletto and Prof. Ian W. Hamley

      Article first published online: 16 AUG 2013 | DOI: 10.1002/anie.201301960

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      Queuing up: Molecular orientation within macroscopically aligned nanotubes of the peptide AAAAAAK can be studied by solid-state NMR and IR spectroscopy. Line shape analysis of the NMR spectra indicates that the peptide N[BOND]H bonds are tilted 65–70° relative to the nanotube long axis. Re-evaluation of earlier X-ray fiber diffraction data suggests that the peptide molecules are hydrogen-bonded in a helical arrangement along the nanotube axis.

    19. Surface Analysis

      Use of In Situ Atomic Force Microscopy to Follow Phase Changes at Crystal Surfaces in Real Time (pages 10541–10544)

      Dr. Ranjit Thakuria, Dr. Mark D. Eddleston, Ernest H. H. Chow, Dr. Gareth O. Lloyd, Barry J. Aldous, Joseph F. Krzyzaniak, Prof. Andrew D. Bond and Prof. William Jones

      Article first published online: 16 AUG 2013 | DOI: 10.1002/anie.201302532

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      AFM of cocrystals: Atomic force microscopy can be used to observe phase changes at crystal surfaces where the transformation is accompanied by a change in the spacing between layers of molecules (see picture). The conversion of a metastable polymorph of the caffeine–glutaric acid cocrystal into the thermodynamically stable form was analyzed continuously in situ using intermittent-contact-mode atomic force microscopy.

    20. Crystal Growth

      Enantiomer-Specific Oriented Attachment: Formation of Macroscopic Homochiral Crystal Aggregates from a Racemic System (pages 10545–10548)

      Prof. Cristóbal Viedma, Prof. J. Michael McBride, Prof. Bart Kahr and Prof. Pedro Cintas

      Article first published online: 14 AUG 2013 | DOI: 10.1002/anie.201303915

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      Let's get together: Racemic samples of d- and l-enantiomorphous NaBrO3 (or NaClO3) crystals aggregate with nearly complete enantioselection. Centimeter-sized enantiopure megacrystals are often produced, and these can be sorted easily.

    21. In Vivo Labeling

      Mesoporous Silica Nanoparticle Pretargeting for PET Imaging Based on a Rapid Bioorthogonal Reaction in a Living Body (pages 10549–10552)

      Sang Bong Lee, Hye Lan Kim, Dr. Hwan-Jeong Jeong, Dr. Seok Tae Lim, Dr. Myung-Hee Sohn and Prof. Dong Wook Kim

      Article first published online: 16 AUG 2013 | DOI: 10.1002/anie.201304026

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      Last-minute labeling: Mesoporous silica nanoparticles (MSNs) were modified with a very short half-life fluorine-18-labeled azide radiotracer by a cycloaddition reaction after the MSNs had reached the tumor site in mice. The tumor could then be visualized successfully with positron emission tomography.

    22. DNA Modification

      You have full text access to this OnlineOpen article
      DNA Modification under Mild Conditions by Suzuki–Miyaura Cross-Coupling for the Generation of Functional Probes (pages 10553–10558)

      Lukas Lercher, Dr. Joanna F. McGouran, Dr. Benedikt M. Kessler, Prof. Christopher J. Schofield and Prof. Benjamin G. Davis

      Article first published online: 13 AUG 2013 | DOI: 10.1002/anie.201304038

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      Quick and clean: A method for Pd-catalyzed Suzuki–Miyaura cross-coupling to iododeoxyuridine (IdU) in DNA is described. Key to the reactivity is the choice of the ligand and the buffer. A covalent [Pd]–DNA intermediate was isolated and characterized. Photocrosslinking probes were generated to trap proteins that bind to epigenetic DNA modifications.

    23. Photochemistry

      Singlet-Oxygen-Sensitizing Near-Infrared-Fluorescent Multimodal Nanoparticles (pages 10559–10563)

      Dr. Edakkattuparambil Sidharth Shibu, Dr. Sakiko Sugino, Prof. Kenji Ono, Hironobu Saito, Ayama Nishioka, Dr. Shohei Yamamura, Prof. Makoto Sawada, Prof. Yoshio Nosaka and Prof. Dr. Vasudevanpillai Biju

      Article first published online: 13 AUG 2013 | DOI: 10.1002/anie.201304264

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      Nanoprobes based on quantum clusters (QC) with near-infrared fluorescence, magnetic-resonance-imaging contrast, and singlet-oxygen-sensitized intracellular fluorescence are studied. The generation of singlet oxygen and singlet-oxygen-sensitized fluorescence uncaging by magnetic and NIR-emitting nanoparticles are exploited for multimodal bioimaging in vitro.

    24. Natural Products

      Biosynthesis of the Antimetabolite 6-Thioguanine in Erwinia amylovora Plays a Key Role in Fire Blight Pathogenesis (pages 10564–10568)

      Dr. Sébastien Coyne, Dr. Cornelia Chizzali, Mohammed N. A. Khalil, Agnieszka Litomska, Dr. Klaus Richter, Prof. Dr. Ludger Beerhues and Prof. Dr. Christian Hertweck

      Article first published online: 22 AUG 2013 | DOI: 10.1002/anie.201305595

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      Sulfur for fire: The molecular basis for the biosynthesis of the antimetabolite 6-thioguanine (6TG) was unveiled in Erwinia amylovora, the causative agent of fire blight. Bioinformatics, heterologous pathway reconstitution in E. coli, and mutational analyses indicate that the protein YcfA mediates guanine thionation in analogy to 2-thiouridylase. Assays in planta and in cell cultures reveal for the first time a crucial role of 6TG in fire blight pathogenesis.

    25. Heterogeneous Catalysis

      Atomically Thin Tin Dioxide Sheets for Efficient Catalytic Oxidation of Carbon Monoxide (pages 10569–10572)

      Dr. Yongfu Sun, Fengcai Lei, Shan Gao, Prof. Bicai Pan, Dr. Jingfang Zhou and Prof. Yi Xie

      Article first published online: 14 AUG 2013 | DOI: 10.1002/anie.201305530

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      The thinner the better: SnO2 sheets that are five atomic layers thick are an efficient catalyst for the oxidation of CO (see picture). These sheets, which have 40 % surface atom occupancy and are fabricated by a scalable ethylenediamine-assisted pathway, show remarkably improved catalytic performances compared to other SnO2 species, with the apparent activation energy lowered to 59.2 kJ mol−1 and the full-conversion-temperature lowered to 250 °C.

    26. Synthetic Methods

      Palladium(II)-Catalyzed Direct Conversion of Methyl Arenes into Aromatic Nitriles (pages 10573–10576)

      Zhibin Shu, Yuxuan Ye, Yifan Deng, Dr. Yan Zhang and Prof. Dr. Jianbo Wang

      Article first published online: 21 AUG 2013 | DOI: 10.1002/anie.201305731

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      From methyl to nitrile: A mild ammoxidation method, which directly converts methyl arenes into aromatic nitriles, has been developed by using Pd(OAc)2 and N-hydroxyphthalimide (NHPI) as the catalysts, and tert-butyl nitrite as the nitrogen source and oxidant.

    27. Synthetic Biology

      Rapid, Isothermal DNA Self-Replication Induced by a Destabilizing Lesion (pages 10577–10581)

      Abu Kausar, Catherine J. Mitran, Yimeng Li and Prof. Julianne M. Gibbs-Davis

      Article first published online: 6 AUG 2013 | DOI: 10.1002/anie.201303225

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      You spin me round: Using a destabilizing abasic site and high concentration of ligase, rapid DNA self-replication in an isothermal ligase chain reaction (LCR) was produced. Both destabilization and rapid ligation are essential for proper LCR replication. This method also provides insight into prebiotic nucleotide replication and is a potential amplification method for biodiagnostics.

    28. Synthetic Methods

      Palladium/Copper-Catalyzed Oxidative C[BOND]H Alkenylation/N-Dealkylative Carbonylation of Tertiary Anilines (pages 10582–10585)

      Renyi Shi, Lijun Lu, Hua Zhang, Borui Chen, Yuchen Sha, Chao Liu and Prof. Aiwen Lei

      Article first published online: 14 AUG 2013 | DOI: 10.1002/anie.201303911

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      C[BOND]H/C[BOND]N activation: The first palladium/copper-catalyzed aerobic oxidative C[BOND]H alkenylation/N-dealkylative carbonylation of tertiary anilines has been developed. Various functional groups were tolerated and acrylic ester could also be suitable substrates. This transformation provided efficient and straightforward synthesis of biologically active 3-methyleneindolin-2-one derivatives from cheap and simple substrates.

    29. Detection of RNA

      Folding of 16S rRNA in a Signal-Producing Structure for the Detection of Bacteria (pages 10586–10588)

      Dr. Yulia V. Gerasimova and Dr. Dmitry M. Kolpashchikov

      Article first published online: 3 SEP 2013 | DOI: 10.1002/anie.201303919

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      Sixty-four DNA strands hybridize to 16S rRNA to form 32 deoxyribozyme catalytic cores that produce a fluorescent signal. The approach allows detection of 0.6 pM 16S rRNA, or about 3×104 bacterial cells in a PCR-free format.

    30. Uranium Chemistry

      Comparison of the Reactivity of 2-Li-C6H4CH2NMe2 with MCl4 (M=Th, U): Isolation of a Thorium Aryl Complex or a Uranium Benzyne Complex (pages 10589–10592)

      Dr. Lani A. Seaman, Elizabeth A. Pedrick, Dr. Takashi Tsuchiya, Dr. Guang Wu, Prof. Dr. Elena Jakubikova and Prof. Dr. Trevor W. Hayton

      Article first published online: 13 AUG 2013 | DOI: 10.1002/anie.201303992

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      Why do U react like that? Reaction of 2-Li-C6H4CH2NMe2 with [MCl4(DME)n] (M=Th, n=2; M=U, n=0) results in the formation of a thorium aryl complex, [Th(2-C6H4CH2NMe2)4] or a uranium benzyne complex, [Li][U(2,3-C6H3CH2NMe2)(2-C6H4CH2NMe2)3]. A DFT analysis suggests that the formation of a benzyne complex with U but not with Th is a kinetic and not thermodynamic effect.

    31. Proteomics

      Bioorthogonal Approach to Identify Unsuspected Drug Targets in Live Cells (pages 10593–10597)

      Dr. Katherine S. Yang, Dr. Ghyslain Budin, Dr. Carlos Tassa, Olivier Kister and Prof. Ralph Weissleder

      Article first published online: 19 AUG 2013 | DOI: 10.1002/anie.201304096

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      A proteomics method to pull down secondary drug targets from live cells is described. The drug of interest is modified with trans-cyclooctene (TCO) and incubated with live cells. Upon cell lysis, the modified drug bound to the protein is pulled down using magnetic beads decorated with a cleavable tetrazine-modified linker. Samples are then run on an SDS-PAGE gel and isolated bands are submitted for mass spectrometry analysis to identify drug targets.

    32. C–H Carbonylation

      Synthesis of Dibenzopyranones through Palladium-Catalyzed Directed C–H Activation/Carbonylation of 2-Arylphenols (pages 10598–10601)

      Dr. Shuang Luo, Dr. Fei-Xian Luo, Xi-Sha Zhang and Prof. Dr. Zhang-Jie Shi

      Article first published online: 12 AUG 2013 | DOI: 10.1002/anie.201304295

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      Dibenzopyranones were synthesized by a palladium-catalyzed phenol-directed C–H activation/carbonylation of 2-phenylphenol derivatives in the presence of CO. Pd(OAc)2 was used as a catalyst and Cu(OAc)2 as a catalytic oxidant in the presence of air.

    33. Coordination Copolymerization

      A One-Pot Synthesis of a Triblock Copolymer from Propylene Oxide/Carbon Dioxide and Lactide: Intermediacy of Polyol Initiators (pages 10602–10606)

      Prof. Dr. Donald J. Darensbourg and Dr. Guang-Peng Wu

      Article first published online: 14 AUG 2013 | DOI: 10.1002/anie.201304778

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      Just add water: The copolymerization of propylene oxide and CO2 catalyzed by a cobalt complex is tolerant to the addition of water as chain-transfer reagent to afford polyols (HO-(PPC)-OH) with narrow molecular weight distributions (see picture; PPC=poly(propylene carbonate); PLA=polylactide). The addition of an organocatalyst to these polyols in the presence of lactides produces well-defined triblock copolymers (PLA-b-PPC-b-PLA).

    34. Kinetic Resolution

      Regioselective Hydroarylations and Parallel Kinetic Resolution of Vince Lactam (pages 10607–10610)

      Dr. Adam S. Kamlet, Cathy Préville, Kathleen A. Farley and Dr. David W. Piotrowski

      Article first published online: 16 AUG 2013 | DOI: 10.1002/anie.201304818

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      Two regioselective and complementary hydroarylation reactions of an unsymmetrical cyclic olefin have been developed. The products can be transformed in one step into constrained γ-amino acids. Regioselective arylation of Vince lactam is controlled by the choice of phosphine ligand enantiomer and the substituent on the amide nitrogen atom. The method was extended to a general regiodivergent parallel kinetic resolution of the racemic lactam.

    35. Heterocycles

      Palladium-Catalyzed Hydrobenzylation of ortho-Tolyl Alkynyl Ethers by Benzylic C[BOND]H Activation: Remarkable Alkynoxy-Directing Effect (pages 10611–10615)

      Yasunori Minami, Kotomi Yamada and Tamejiro Hiyama

      Article first published online: 16 AUG 2013 | DOI: 10.1002/anie.201304893

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      It's selective: The title reaction involves palladium(0)-catalyzed insertion of C[TRIPLE BOND]C bonds into benzylic C(sp3)[BOND]H bonds, thus providing efficient access to 2-methylene-2,3-dihydrobenzofurans, which transform into benzofurans upon treatment with a weak acid (e.g., AcOH) and electrophiles. The alkynoxy group serves as a directing group in promoting C[BOND]H bond functionalization.

    36. Lipopeptides

      Direct Peptide Lipidation through Thiol–Ene Coupling Enables Rapid Synthesis and Evaluation of Self-Adjuvanting Vaccine Candidates (pages 10616–10619)

      Tom H. Wright, Dr. Anna E. S. Brooks, Alicia J. Didsbury, Dr. Geoffrey M. Williams, Dr. Paul W. R. Harris, Prof. Dr. P. Rod Dunbar and Prof. Dr. Margaret A. Brimble

      Article first published online: 12 AUG 2013 | DOI: 10.1002/anie.201305620

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      A radical lipidation: Application of a novel thiol–ene lipidation enables the one-step synthesis of self-adjuvanting antigenic peptides as vaccine candidates. The resultant monoacyl lipopeptides are shown to activate monocytes in a robust manner.

    37. Gas Separation

      Tuning Anion-Functionalized Ionic Liquids for Improved SO2 Capture (pages 10620–10624)

      Guokai Cui, Junjie Zheng, Xiaoyan Luo, Wenjun Lin, Fang Ding, Prof. Haoran Li and Prof. Congmin Wang

      Article first published online: 12 AUG 2013 | DOI: 10.1002/anie.201305234

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      You can have your cake and eat it too: A “dual-tuning” strategy for improving the capture of SO2 was developed by introducing electron-withdrawing sites on the anions to produce several kinds of functionalized ionic liquids. Those functionalized with a halogen group exhibited improved performance over their non-halogenated counterparts, leading to highly efficient and reversible capture.

    38. DNA Trapping

      One-step Preparation of Macroporous Polymer Particles with Multiple Interconnected Chambers: A Candidate for Trapping Biomacromolecules (pages 10625–10629)

      Qiuping Qian, Xiaopeng Huang, Xinyue Zhang, Prof. Zhigang Xie and Prof. Yapei Wang

      Article first published online: 12 AUG 2013 | DOI: 10.1002/anie.201305003

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      Taking advantage of photothermal conversion, the surface pores of water-dispersible single-walled carbon nanotubes assembled on polymer particles were rapidly closed by NIR irradiation to produce macroporous polymeric microspheres with multiple interconnected chambers. These particles can act as smart containers to encapsulate and hold DNA molecules.

    39. Asymmetric Catalysis

      Rhodium-Catalyzed Dynamic Kinetic Asymmetric Transformations of Racemic Allenes by the [3+2] Annulation of Aryl Ketimines (pages 10630–10634)

      Duc N. Tran and Prof. Dr. Nicolai Cramer

      Article first published online: 16 AUG 2013 | DOI: 10.1002/anie.201304919

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      Racemization required: Rhodium(I)-catalyzed C[BOND]H activation directed by unprotected ketimines initiates selective [3+2] cycloaddition with allenes, providing access to highly substituted indenylamines. The reaction proceeds through the dynamic kinetic asymmetric transformation of racemic allenes. The catalyst controls the enantio- and diastereoselectivity, the regioselectivities of the C[BOND]H activation and allene incorporation, as well as the E/Z ratio.

    40. Simultaneous Catalysis

      Harnessing Reversible Oxidative Addition: Application of Diiodinated Aromatic Compounds in the Carboiodination Process (pages 10635–10638)

      David A. Petrone, Matthias Lischka and Prof. Dr. Mark Lautens

      Article first published online: 12 AUG 2013 | DOI: 10.1002/anie.201304923

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      An I for an I: Conditions for the intramolecular carboiodination and the simultaneous convergent intramolecular carboiodination/intermolecular Heck reaction of various diiodoarenes were developed. The ability of the Pd0/QPhos catalyst/ligand combination to undergo reversible oxidative addition allows these reactions to proceed well, thus increasing both the appeal and utility of this class of substrates in site-selective cross-coupling reactions.

    41. Conjugate Addition

      Acid-Catalyzed Direct Conjugate Alkenylation of α,β-Unsaturated Ketones (pages 10639–10643)

      Dr. Kazuhiro Okamoto, Eisuke Tamura and Prof. Dr. Kouichi Ohe

      Article first published online: 12 AUG 2013 | DOI: 10.1002/anie.201305188

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      New tricks, old reaction: The title reaction proceeds under mild and transition-metal-free conditions (see scheme; Tf=trifluoromethanesulfonyl). Various combinations of substrates are applicable to the synthesis of γ,δ-unsaturated ketones by employing silicon substituents at the β-position of the enones. The silicon substituents play a key role in stabilization of the cationic intermediate by hyperconjugation.

    42. Synthetic Methods

      Highly Enantioselective γ-Amination by N-Heterocyclic Carbene Catalyzed [4+2] Annulation of Oxidized Enals and Azodicarboxylates (pages 10644–10647)

      Xiang-Yu Chen, Fei Xia, Jin-Tang Cheng and Prof. Dr. Song Ye

      Article first published online: 13 AUG 2013 | DOI: 10.1002/anie.201305571

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      γ-Amination: The title reaction was developed to give the corresponding dihydropyridazinones in good yields with excellent enantioselectivities (see scheme; Mes=2,4,6-trimethylphenyl). The annulation reaction worked well for γ-aryl, γ-alkyl, or γ-alkenyl oxidized enals. Highly enantiopure tetrahydropyridazinones and γ-amino acid derivatives could be easily prepared by chemical transformations of the resulting dihydropyridazinones.

    43. Reactive molecules

      Predicting Kinetically Unstable C[BOND]C Bonds from the Ground-State Properties of a Molecule (pages 10648–10651)

      Dr. Georgios Markopoulos and Prof. Jörg Grunenberg

      Article first published online: 14 AUG 2013 | DOI: 10.1002/anie.201303821

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      Determining the weakest link: A simple analysis pinpoints kinetically unstable carbon–carbon bonds. No prior knowledge of reaction pathways is necessary and the approach is particularly helpful for the prediction of novel molecules. krel=relaxed force constant, req=bond length.

    44. Polymers as Vaccines

      Water-Soluble Polymers Coupled with Glycopeptide Antigens and T-Cell Epitopes as Potential Antitumor Vaccines (pages 10652–10656)

      Lutz Nuhn, Sebastian Hartmann, Björn Palitzsch, Dr. Bastian Gerlitzki, Prof. Dr. Edgar Schmitt, Prof. Dr. Rudolf Zentel and Prof. Dr. Horst Kunz

      Article first published online: 26 AUG 2013 | DOI: 10.1002/anie.201304212

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      Highly decorated: Tumor-associated MUC1 glycopeptide and tetanus toxoid T-cell epitope P2 can be attached to water-soluble poly(N-(2-hydroxypropyl)methacrylamide) carriers by orthogonal ligation techniques. Fully synthetic vaccine A with additional nanostructure-promoting domains induced antibodies that exhibit high affinity to tumor cells.

    45. :BR CO Co-catenation

      Phosphine-Triggered Co-catenation of :BR and CO on an Iron Atom (pages 10657–10660)

      Prof. Dr. Holger Braunschweig, Dr. Qing Ye, Dr. Alfredo Vargas, Dr. Krzysztof Radacki and Dr. Alexander Damme

      Article first published online: 23 AUG 2013 | DOI: 10.1002/anie.201304972

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      The chain gang: By treatment of an iron bis(borylene) complex with PCy3 and subsequent stepwise substitution of a CO ligand by PMe3, a catenated 1D OC-B-B-CO chain was generated in the coordination sphere of iron. This is an CO analogue of the recently reported 1D B-B-B-B chain in the iron tetraboron complex [(OC)2Fe{BN(SiMe3)2}2(BDur)2]. Dur=2,3,5,6-tetramethylphenyl.

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